Travel Itinerary: A Guy’s Weekend in OC with Pilot Drew

11 a.m.: Check in to your hotel

It doesn’t get much better than the SeaLoft Oceanfront Hotel for a home base. Enjoy amazing views and relaxed, coastal vibes at this seaside hotel. You’re right next to some of OCMD’s best restaurants, and being just steps from the beach means you can fall asleep to the sound of the ocean every night.

12 p.m.: Feast at a local crab house

Make your first stop, Assateague Crab House, and go all in on a dozen large crabs to share with your crew. When you’re in Maryland, it’s a must and the perfect way to settle into that OC mindset.

2 p.m.: Paddle Through Nature

Next up, a self-guided kayak tour through the scenic backwaters of Assateague Island National Seashore with Assateague Adventures. Even with a little rain, you can still take in the peaceful surroundings and enjoy some unforgettable views.

6 p.m.: Dinner on the Dock

For dinner, head to Harrison’s Harbor Watch, an Ocean City staple. Known for its outstanding raw bar and stunning inlet views, this spot serves seafood so fresh, it’s like a reminder you’re right on the coast.

7:40 p.m.: Sunset Boat Ride with Sea Rocket

Watch the sun set over the Ocean City skyline while floating in the beautiful Atlantic Ocean and Assawoman Bay aboard the Sea Rocket!

9 p.m.: Late Night Views & Vibes

Cap off the night at Spain Wine Bar, recently voted Maryland’s best rooftop bar. Located atop of the Cambria Hotel, this spot definitely lives up to the hype, and the flourless chocolate cake paired with a signature cocktail is the perfect end to the night.

8:30 a.m.: Fuel Up at Playa Bowls

Kick off your day with a healthy and energizing breakfast at Playa Bowls, offering acai bowls, smoothies, and coffee to keep you going strong for whatever adventure OCMD has for you.

10:30 a.m.: Morning Teeing off on the Greens

Recognized as one of the most beautiful courses in the Mid-Atlantic, Ocean City Golf Club won’t disappoint. The greens are pristine, and even if you only hit it straight a few times, it can still count as a win.

Afternoon: Just for Bragging Rights

Swing by Jolly Roger Amusement Park for some lighthearted competition. Pro tip: challenge your brother to the same game so at least one of you will walk away with a prize.

5 p.m.: Sunset Dining

From live music at the iconic Fager’s Island to a fine dining experience that’ll blow you away, this dinner hits every note with great food and a great atmosphere paired with the perfect OCMD sunset.

9 a.m.: Bayfront Breakfast

Start your morning at The Angler, a local landmark for over 85 years. You’ll get a hearty breakfast paired with unbeatable views of the bay.

11 a.m.: Crafted on the Coast

Seacrets Distilling Company is known for its nightlife, and the distillery tour is the real hidden gem. You’ll walk through the facility and learn about its rich history, with thoughtful details that bring the past to life. And of course, you’ll get to sample some incredible house-made spirits.

1 p.m.: Farewell Feast

Wrap up the trip with one last seafood stop at Crab Alley. Enjoy laid-back vibes, classic Maryland flavors, and a final taste of the coast before heading home.

Afternoon: Pack Up & Head Out

After a memorable three-day getaway, Ocean City bids farewell for now. From fresh seafood and rooftop views to peaceful paddles and lively boardwalk games, the charm of this coastal town sticks with you long after you’ve left. But don’t worry, the beach, the bay, and all the fun in between will be waiting next summer.

Ocean City, Maryland - Somewhere to Smile About.